Copperable disazo dyestuffs



Patented Aug. 18, 1959 As l-aryl 3-methyl amino-pyrazo1s there may be 2,900,379 mentioned, for example, l-(8'-, 7-, 6".-, 5'- or 4'-mono- COPPERABLE DISAZO DYESTUFFS I sulfonaphthyl-wl -me hy r pyrazo 1'-,( o

4' carboxynaphthyl [2' 1) 3 methyl 5 '-'aminopyra- Klaus Biickmann, Koln-Stammheim, and Carl Taube, 5 Z01 1 pheny1 3 methyl s aminopyrazol, 1 3 or 4 Leverkusen-Bayerwerk, Germany, assignors to Farbenchlorophenyl) 3 methyl s aminopyrazol, or fabriken Bayer laktleugesellschaft, Leverk usen, Gernitr oph eny1) 3 methyl s aminopyrazol, or many a corporate of Germany v or -alkoxyphenyl)-3-methyl-5-aminopyrazo1, 1-(3- or No Drawing. Application June 25, 1957 4' aminophenyl or acetylarninophenyl) 3 methyl 5- Serial N0. 667,960 aminopyrazol, or 1-(3- or 4-sulfoor -sulfamidopheny1)- 3-meth l-S-amino razol. Claims Pnonty apphcanon Germany August 195 The iiew disaz dyestufis dye cotton and regenerated 3 Claims. (Cl. 260-161) cellulose in reddish violet shades which become very fast to light and, to washing by after-treatment with copperyielding agents.

The present invention relates to new copperable dis- The following examples are given for the purpose of azo dyestuffs; more particularly it relates to disazo dyeillustrating the invention without, however, limiting it stufis corresponding to the formula thereto:

CH IC(I?N=N N=N- m 0 nos Nai NH R N H00 3 n I 0003 I R wherein R and R stand for aryl radicals. 3o 1 1 Examplal The new disazo dyestufls are obtainable bycoupling 1 mol of tetrazotized 4,4'-diamino diphenyl-3,3'-dicarboxylhc g g of i m g'g of water. Into this solution there are introduced 17.3 mm an m0 0 an lirea o m ygrams of l-phenyl-3-methyl-5-aminopyrazol dissolved droxynaphthalene-7-sulfonie acid. h hl d 2- mint es of Water The The urea derivatives of the 2-amino-5-hydroxynaph- W y 06 one an m r 27.2 grams of 4,4 diaminodiphenyl-3,3 '-dicarbo iylic acid are tetrazotized in usual manner in 500 millilitres thalene-7-sulfonic acid may be prepared, for instance, by Soluuon 1S mndered' of by adding Sodmm treating a solution of 2 amino 5 hydroxynaphthalene;7 acetate and stirred overmght. The separated dlazo monolf i acid and a Suitable arylamine, for e m azo compound is filtered and poured into a soda-alkaline 1 1 i 4- i 2 amin0naphtha1ene 40 solution of 48.8 grams of the urea obtamed by phosgena- 8-sulfonic acid, with phosgene. Further arylarnines suittion of 2'ami110'5'hydYOXyllaphthalene-7-slllfonic acid and able for the urea formation with 2-amino-5-hydroxynaph- 2-aminonaphthalene 8 sulfonic acid in 500 millilitres of thalene-7-sulfonic acid are, for example, aminobenzene, water. When the coupling is completed, the disazo dyeaminobenzene carboxylic acids, Z-aminonaphthalene: ,stuif is isolated and dried. It corresponds to the formula or -.4-sulfonic acid or 2-aminonaphthalene-6-carboxy1ic and represents a water-soluble dark powder which dyes acid. cotton and regenerated cellulose in reddish violet shades;

The urea-group containing coupling compounds can The dyeing becomes very fast to light andvto washing also be obtained by reacting an urethane of the Z-aminoby after-treatment with copper-yielding agents.

5-hydroxynaphthalene-7-sulfonic acid with an arylamine according to the process described in German Patent Example 2 871,000. The diazo monoazo compound prepared according the method described in Example 1 from 27.2 grams of tetrazotized' 4,4-diaminodiphenyl-3,3-dicarboxylic acid and 17.3 grams of l-phenyl-3-methyL5-aminopyrazol is coupled in a soda-alkaline medium with 41.5 grams of the urea prepared by phosgenation of Z-amino-S-hydroxynaphtha1ene-7-sulfonic acid and l-acetylaminol-aminobenzene. The disazo dyestufi thus obtained is, after drying, a water-soluble dark-brown powder which dyes cotton and regenerated cellulose in red violet shades. The dyeing becomes very fast to light and to washing by aftertreatment with copper-yielding agents.

Example 3 27.2 grams of 'tetrazotized .4.4':-diaminodiphenyl-3,3'- dicarboxylic acid are combined with 30.3 grams of l-(8'- sulfdnaphthyl-[Zf])13-methyl5-aminopyrazol. The diazo monoazo compound thus obtained is coupled with'41.5

grams of the urea which was obtained by phosgenation of Z-amino-5-hydroxy-naphthalene-7-sulfonic acid :and -1-acetylamino-4-aminobenzene. The isolated dyestuff represents adarkpowder -which'is soluble in water. It

dyes cotton and regenerated'celhilose in red violet shades which become very fastto light-by after-coppering.

Example 4 0.2 grams of the dyestufi obtained according to Example 1 are dissolved in 200 ml. of hot water with the addition of 1 gram of soda. In this solution there are introduced 10 grams of a cotton fabric. The bath is heated to 95 C. and maintained at this temperature with stirring for 1 hour while adding in portions 2 grams of a 10 percent sodium sulfate solution. After rinsing with water the dyed material is after-treated at 80-90 C. within 20 to 30 minutes in a bath containing 0.3 grams of crystalline copper sulfate and 0.1 gram of acetic acid in 200 ml. of water, whereby the reddish violet dyeing becomes very fast to light and to washing.

We claim:

1. A copperable disazo dyestufi conresponding to the formula wherein R and'R each stand for an aryl radical selected from the group consisting of the benzene and naphthalene series.

2. The .disazo dyestufi corresponding to the formula GOOH 3. I-he-disazodyestufi corresponding to the formula References Citedin the 'file ofthis'p'atent UNITED STATES PATENTS Morschel et al. Dec. 6, 1955 

1. A COPPERABLE DISAZO DYESTUFF CORRESPONDING TO THE FORMULA 